Sodium Cyanide → HCID 21447365, compound

HRID 597284Notes

Reaction equation

HRID 597284 reaction equation
Cl[CH2:2][C:3]1[C:11]2[O:10][CH:9]=[C:8]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)[C:7]=2[CH:6]=[CH:5][CH:4]=1.[C-:19]#[N:20].[Na+]>CC(C)=O.C(O)C.O>[C:19]([CH2:2][C:3]1[C:11]2[O:10][CH:9]=[C:8]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)[C:7]=2[CH:6]=[CH:5][CH:4]=1)#[N:20]

Participants

6

Reactant 2

HCID 8929Sodium CyanideHCID 21447364HCID 21447364, compound

Product 1

HCID 21447365HCID 21447365, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 7-chloromethyl-3-(4-fluorophenyl)benzofuran (130.3 g., 0.50 mole) in acetone (750 ml.) and ethanol (500 ml.) is added a solution of sodium cyanide (39.5 g., 0.50 mole) in water 150 ml.). The mixture is heated to its reflux for 5 hours. The mixture is then evaporated in vacuo to concentrate it. The residue is dissolved in dichloromethane, then washed thoroughly with water, dried and concentrated by evaporation in vacuo. The oily residue is recrystallized twice from cyclohexane, then deposited on 70 g. of a magnesium silicate material used for elution chromatography and chromatographed on 400 g. of the silicate type column. Elution with hexane, benzene-hexane (1:4), (1:1) and (3:2), followed by benzene gives the desired product, 7-cyanomethyl-3-(4-fluorophenyl)benzofuran, in the benzene fractions.

Workup

  1. temperatureThe mixture is heated to its
  2. temperaturereflux for 5 hours
  3. customThe mixture is then evaporated in vacuo
  4. concentrationto concentrate it
  5. dissolutionThe residue is dissolved in dichloromethane
  6. washwashed thoroughly with water
  7. customdried
  8. concentrationconcentrated by evaporation in vacuo
  9. customThe oily residue is recrystallized twice from cyclohexane
  10. washof a magnesium silicate material used for elution chromatography
  11. customchromatographed on 400 g
  12. washElution with hexane, benzene-hexane (1:4), (1:1) and (3:2)

Sources & evidence

ORD record
ord-b8b8d49f0e1d4202bd2fd98eee24c5d7
Source dataset
uspto-grants-1977_03
Patent number
US04013692

Reaction notes

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